25083-11-8

Usage

Classification

Derivative of indole, belongs to the class of indole alkaloids.

Physical state

Pale yellow solid at room temperature.

Usage

Commonly used as a building block in organic synthesis for producing various pharmaceuticals and biologically active compounds.

Potential medical applications

Studied for its potential as an antipsychotic and anti-inflammatory agent.

Medical approval

Not approved for any specific medical use.

Safety precautions

Should be handled and used with caution due to potential health hazards and toxicity.

Upstream product

• 73425-20-4 1-phenylindoline-2-thione 
• 496-15-1 1-indoline 
• 108-90-7 chlorobenzene 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 2039-87-4 2-chlorostyrene 
• 930-68-7 cyclohexenone 
• 66003-76-7 Diphenyliodonium triflate 
• 144930-50-7 mesityl(phenyl)iodonium triflouromethanesulfonate 
• 6293-66-9 diphenyliodonium p-toluenesulfonate 
• 16668-99-8 bis(phenyl)iodonium trifluoroacetate 
• 615-42-9 1,2-Diiodobenzene 
• 16096-33-6 1-phenyl-1H-indole 
• 100-68-5 methyl-phenyl-thioether 
• 591-50-4 iodobenzene 

Downstream Products

• 16096-33-6 1-phenyl-1H-indole 
• 1443380-72-0 C₁₇H₁₇N 
• 1443380-57-1 C₂₄H₃₁N₃O₄ 
• 1359859-55-4 C₂₃H₂₇NO₄ 

Relevant academic research and scientific papers

Covalent Organic Frameworks toward Diverse Photocatalytic Aerobic Oxidations

Photoactive two-dimensional covalent organic frameworks (2D-COFs) have become promising heterogenous photocatalysts in visible-light-driven organic transformations. Herein, a visible-light-driven selective aerobic oxidation of various small organic molecules by using 2D-COFs as the photocatalyst was developed. In this protocol, due to the remarkable photocatalytic capability of hydrazone-based 2D-COF-1 on molecular oxygen activation, a wide range of amides, quinolones, heterocyclic compounds, and sulfoxides were obtained with high efficiency and excellent functional group tolerance under very mild reaction conditions. Furthermore, benefiting from the inherent advantage of heterogenous photocatalysis, prominent sustainability and easy photocatalyst recyclability, a drug molecule (modafinil) and an oxidized mustard gas simulant (2-chloroethyl ethyl sulfoxide) were selectively and easily obtained in scale-up reactions. Mechanistic investigations were conducted using radical quenching experiments and in situ ESR spectroscopy, all corroborating the proposed role of 2D-COF-1 in photocatalytic cycle.

Double Ligands Enabled Ruthenium Catalyzed ortho-C?H Arylation of Dialkyl Biarylphosphines: Straight and Economic Synthesis of Highly Steric and Electron-Rich Aryl-Substituted Buchwald-Type Phosphines

A double-ligands enabled ruthenium catalyzed C(sp2)?H arylation of dialkyl phosphines is described, which provides a straight access to aryl-substituted dialkyl phosphine ligands. The combination of 1,3-diketone and amino acid ligands is essential for this transformation. An important six-membered cycloruthenium intermediate was successfully isolated and characterized by X-ray diffraction. Mechanistic studies showed that the 1,3-diketone promoted the process of oxidative addition of cycloruthenium intermediate. Some of modified CyJohnPhos ligands exhibited highly catalytic activity in palladium catalyzed C?N bond formation. (Figure presented.).

Dual Photoredox/Cobaloxime Catalysis for Cross-Dehydrogenative α-Heteroarylation of Amines

We report a dual-catalytic platform for the cross-dehydrogenative-coupling between (benzo-)thiazoles and amines which combines low loadings of an iridium photoredox catalyst and a cobaloxime catalyst under blue light irradiation. This transformation occurs without stoichiometric oxidants, giving products in moderate to excellent yields. DFT calculations support the key role of Co(II) for rearomatization of the radical-addition intermediate to generate the product.

Nickel-Catalyzed Amination of Aryl Thioethers: A Combined Synthetic and Mechanistic Study

Herein, we report a nickel-1,2-bis(dicyclohexylphosphino)ethane (dcype) complex for the catalytic Buchwald-Hartwig amination of aryl thioethers. The protocol shows broad applicability with a variety of different functional groups tolerated under the catalytic conditions. Extensive organometallic and kinetic studies support a nickel(0)-nickel(II) pathway for this transformation and revealed the oxidative addition complex as the resting state of the catalytic cycle. All the isolated intermediates have proven to be catalytically and kinetically competent catalysts for this transformation. The fleeting transmetalation intermediate has been successfully synthesized through an alternative synthetic organometallic pathway at lower temperature, allowing for in situ NMR study of the C-N bond reductive elimination step. This study addresses key factors governing the mechanism of the nickel-catalyzed Buchwald-Hartwig amination process, thus improving the understanding of this important class of reactions.

Photoinduced Cross-Coupling of Amines with 1,2-Diiodobenzene and Its Application in the Synthesis of Carbazoles

A facile and efficient process for the preparation of various tertiary aminobenzenes and carbazole derivatives via photoinduced cross-coupling of amines with 1,2-diiodobenzene is reported. Mechanistic investigations indicate that the transformation proceeds via nucleo-philic addition of an amine to the benzyne intermediate accompanied with a proton transfer process, followed by an oxidative cyclization of the generated diphenylamine to furnish the corresponding carbazole products.

N-Arylamines Coupled with Aldehydes, Ketones, and Imines by Means of Photocatalytic Proton-Coupled Electron Transfer

A photoredox-catalyzed umpolung strategy for coupling reactions between aldehydes, ketones, imines, and N-arylamines is reported. These reactions proceed by a Br?nsted acid-activated proton-coupled electron transfer pathway, and the protocol was used to synthesize a broad scope of 1,2-amino alcohols and vicinal diamines, both of which are common motifs in biologically active natural products, pharmaceutically active molecules, and ligands.

Direct Acylation of C(sp3)-H Bonds Enabled by Nickel and Photoredox Catalysis

Using nickel and photoredox catalysis, the direct functionalization of C(sp3)-H bonds of N-aryl amines by acyl electrophiles is described. The method affords a diverse range of α-amino ketones at room temperature and is amenable to late-stage coupling of complex and biologically relevant groups. C(sp3)-H activation occurs by photoredox-mediated oxidation to generate α-amino radicals which are intercepted by nickel in catalytic C(sp3)-C coupling. The merger of these two modes of catalysis leverages nickel's unique properties in alkyl cross-coupling while avoiding limitations commonly associated with transition-metal-mediated C(sp3)-H activation, including requirements for chelating directing groups and high reaction temperatures. Teamwork: The direct functionalization of C(sp3)-H bonds of N-aryl amines by acyl electrophiles is achieved, thus affording a diverse range of α-amino ketones at room temperature. C(sp3)-H activation occurs by photoredox-mediated oxidation to generate α-amino radicals which are intercepted by nickel in catalytic C(sp3)-C coupling.

Metal-free N-arylation of indolines with diaryliodonium salts

The N-arylation of indolines using diaryliodonium salts as electrophilic arylating reagents is described. Without the use of any additional additives, the desired N-aryl indolines could be obtained in up to 85% yield.

Modular Synthesis of Biaryl-Substituted Phosphine Ligands: Application in Microwave-Assisted Palladium-Catalyzed C-N Cross-Coupling Reactions

Biaryl-substituted monophosphine-based ligands have been synthesized by transition-metal-free "ARYNE" cross-coupling reaction of aryllithiums with 1,2-dibromobenzene and subsequent regioselective functionalization through bromine-lithium interconversion. These ligands were employed in palladium-catalyzed C-N bond-forming reactions. The reaction was found to be general with wide substrate applicability. A wide variety of both primary and secondary amines were successfully coupled with an array of differently substituted halobenzenes under microwave irradiation to give the expected products in good to excellent yields. A number of biaryl-substituted phosphine ligands screened for the coupling reaction showed that steric bulk and the electronic properties of substituents on phosphorus play a crucial role in governing the catalytic activity of C-N cross-coupling reactions. Biaryl-substituted monophosphines have been synthesized by transition metal free ARYNE cross-coupling reactions and subsequent regioselective functionalization through bromine-lithium interconversion. These ligands were employed in palladium-catalyzed C-N bond-forming reactions.

Palladium-catalyzed annulation of diarylamines with olefins through C-H activation: Direct access to N-arylindoles

A palladium-catalyzed dehydrogenative coupling between diarylamines and olefins has been discovered for the synthesis of substituted indoles. This intermolecular annulation approach incorporates readily available olefins for the first time and obviates the need of any additional directing group. An ortho palladation, olefin coordination, and β-migratory insertion sequence has been proposed for the generation of olefinated intermediate, which is found to produce the expected indole moiety.